Cofounder of CodeCombat and Skritter, experimenter of self, student of rationality, hacker of motivation. One summer I wrote a book, learned to skateboard and throw knives and lucid dream, trained for a marathon and other feats, learned a ton of Chinese.

Watch out: I use "I" 54 times in this post, so this will be boring if you, like me, aren't interested in hearing me talk about myself.

When I was in high school, I was so shy that I couldn't talk to almost anyone outside my family. Through a last-ditch effort when I went to college, I got better. I then got lucky and succeeded at a lot of things I tried after that, which rescued my general confidence, and I did some focused practice, rejection therapy, public speaking, and Beeminding to fix my social confidence.

But even though I'm no longer afraid to try, that doesn't mean that I can do it well. I still feel that I'm not usually a good conversationalist. I haven't had enough practice, especially since I have always spent most of my working time hacking in my lair instead of working socially. I started to practice things like this after the CFAR workshop in March, but put it on hold after getting married when I hurt my feet.

I'm finally recovered and can go outdoors again, so I spent this week practicing: three days of the hallway track at someconferences (plus moderating a discussion), two group classes, a social lunch, a party, hosting my cofounders for hacking, and a few video calls. I'm not completely socially exhausted--yeah, I threw the "introvert" label out of my identity a while ago--but I'm also not going to the second party tonight.

How did it go? I was trying to practice three things:

Be into others' stuff.

Smile.

Be vulnerable instead of safe.

In practice, I usually forgot about #2 and #3. I did much better at trying to focus on other peoples' interests in conversation than I usually do. I'm normally terrible at that, blathering on about my own stuff even as I'm bored of what I'm saying.

One thing I was doing a few months ago was explicitly asking people, right after I talked to them, how I could improve my conversation skills. I would send it in an email so that they could ponder it more and not be as nervous about telling me how I suck. It worked well. People said things like:

I don't smile much, even when I'm engaged, and even when I'm talking about trying to remember to smile more.

I'm not funny enough, and not as funny in person as in writing. (I'm funny in writing?)

I use swearing and exaggerated enunciation as a crutch instead of finding better words.

I talk too much instead of inviting others to speak.

Before I started asking people, this was what I thought I was missing:

I didn't ask more than a handful of people, and it occurs to me that I should start doing this again when meeting new people. It also occurs to me to ask you, dear reader! If you have talked to me and have ideas for how I can become a better conversationalist, please tell me. Critical feedback is way better than me guessing. Then next time you talk to me, it'll be more fun for both of us.

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I would have never thought to do ask this question, but you seem to be getting great feedback.

I've been experimenting with asking questions and listening to others, and not providing my input unless asked. An interesting result is that almost no one asks for my input. In other words, after I listen to them talk about their weekend, they never ask me about mine.

This is a great point and one that I find incredibly annoying. This recently happened on a plane when I patiently listened to a lady's life history. Once she finished, she simply opened her book back up and ignored me for the rest of the trip.

I felt it was extremely rude, but my thoughts were that they fault fell with her instead of myself. Just because someone else is a sub-par listener or conversationalist doesn't necessarily mean that you should strive for the same. You wouldn't stop instilling good manners into your kids just because someone else's were ruining a restaurant, so it's another one of those "take the higher road" moments.

Plus, with an attitude like that, would she have really listened to anything I said anyway?

Ah, that's very interesting. The caveat to all of this is that conversation environments can be very different, so that some things seem to be more or less effective because of it. East coast conversation styles are much different than the west coast. Your industry probably has slightly different conversational norms as well. And too, whether you are speaking to a person with a typically female conversational style or a male one.

Cofounder of CodeCombat and Skritter, experimenter of self, student of rationality, hacker of motivation. One summer I wrote a book, learned to skateboard and throw knives and lucid dream, trained for a marathon and other feats, learned a ton of Chinese.

Thanks for all the feedback, guys! One thing I noticed was how unused I am to taking direct criticism, however nice and constructive. This is a weakness that I thought I would have more time to get over.

Guess I will practice momentarily, though, since I am about to be criticized on stage by Paul Graham and Sam Altman at Startup School office hours tomorrow. I'll, uhh... try to smile.

I have talked to you in person although not recently, as you know. The helpful comment I will give is this--just be yourself. Yes, that sounds like some kind of happy, chirpy advice but you even start this blog post by mentioning that the readers might not be interested. If we weren't we wouldn't be reading it. I have always found you to be interesting and charming in person and well worth the conversation. I am certain others are speaking to you because they also enjoy your company. Be where you are. Be who you are. Don't overthink it. Just talk to people. And yes, you're funny in writing. Quite funny, depending on the topic. -- Cathy Tenzo

This is a concern I have for myself; I'm particularly miserable at telling stories. But, I have plenty of smiles to pass out, and that usually helps. Who knows what the people I talk to think.

My biggest piece of advice is to be genuine in your conversations. That is my preference, at least. I want to engage with people who are kind, and who care about who I am and about themselves (self-deprecating doesn't generally win me over). Being genuine won't help you become a politician--the generally loved sort. But, it will earn you respect and a place at my table.

There are two groups of people that I personally look upon with admiration when it comes to being able to carry fun, interesting dialogue--largely because I think their profession makes them fun, interesting _people_. (Conversation is an externalization of the person, so when you talk about changing the way you make conversation, you talk about changing yourself). Anyway, two groups of people. I say, find a gang of them and hang around. Take mental notes. What's more, enjoy. Here they are:

First, philosophers (or physicists... I think they are sort of the same people). Philosophers are contemplative. They have opinions. They play at arguments--all the time. They are self-aware and have a strong sense of irony and hypocrisy and generally know how to have a good, reflexive laugh at any situation. The philosophers I used to know would have daily gatherings at the pub or at someone's house just to be convivial conversationists.

Second, cultural ethnographers. Ethnographers are trained to care deeply about people. They are trained to find them completely foreign and fascinating, as keepers of unique life perspectives worth teasing out. They learn how to build respectful, insightful, meaningful conversations with strangers. They have to synthesize meanings on the fly. They make a living by retelling mundane stories in a way that is completely captivating and revelatory. (I appreciate the comment made about Terry Gross. She's not an ethnographer, but she is acting rather like one.) If you can't find some ethnographers to befriend, then have a helping of the literature that ethnography students read about how to conduct interviews and how to report findings.

One final thought. I am currently reading about the ethics of dialogue. Levinas, Buber, and Bakhtin. These may not be pragmatic resources, but they'll certainly help you reconsider what a conversation _ought_ to be.

We only spoke once, so take this for what it's worth. We met at the Quantified Self Conference last year. I was going to give a talk about SuperMemo that I thought you'd be interested in. Honestly, you seemed distracted and uninterested, and I didn't expect you to show up. So, I was pleasantly surprised when you did and we talked afterward. I assumed at the point that you may just be someone who I find hard to read.

Here are three things that I have done to help me in conversations. The first is, if I want to talk about something, I ask the other person their thoughts on the topic first. For instance, if I want to tell someone at work about my weekend, I ask about their weekend, and usually they'll then ask about mine. Even though this is a trick to allow me to talk about myself, that thing that I like about it is often, I will get interested and ask questions about what the other person says, and not care as much about what I wanted to say.

As someone said earlier, a good practice is to let people finish speaking. It's incredibly annoying to be cut off when you haven't finished your thought, so keeping quiet until they are done signals that you respect what they are saying.

The third is something that I'm still working on and that is to get into the practice of summarizing and repeating the person's point back to him/her. It causes you to listen more intently (and makes you less focused on what you want to say), and it lets the other person know that you were paying attention (making them feel important). Gary Wolf does this well, a result, I assume, of his background as a journalist.

Of course, to make this work, you have to be genuine in your interest and not seem like someone who is merely applying tricks. An example I can cite is an old co-worker who would ask me about my weekend, and five words into my response, he would jump into what he did on his.

Like you, I started off extremely shy and then had to work my way out of it through practice. Once I beat that demon, there was the challenge of having people actually enjoy talking to me, which is much harder. There were 2 things that really worked for me.

1. I developed a self-depreciating sense of humor. I'm not sure exactly why this works, but people tend to be much more comfortable around me when I make fun of myself. It's a great ice-breaker and almost immediately endears them to me. It works best with little things though: "I would have been here on time, but my GPS is smarter than I am!" If you go too far to the other side, it can make things even more uncomfortable: "I would have been here on time, but I have a massive case of the trots!"

2. I started listening to people...instead of just waiting for my turn to talk. I used to catch a word or two in their statement that related to a story that I wanted to tell, so I would just wait for a long enough pause to interject my thoughts. Now, I actually try to engage in their side of the story. I ask questions about what they're talking about instead of interjecting how it relates to me. If my story is truly relevant, the opportunity to tell it will still be there after they're done. If it's not, then I'm avoiding interrupting for the sake of talking.

Just my $0.02. After working on it for 15 years, I'm still not totally comfortable in social settings, but I have become a decent conversationalist over that time. Hopefully, this helps.

Ask people lots of questions. Seek to really understand something that they care about, or something relevant to them (and hopefully interesting to you). Pretend you're going to be tested on it. Listen to Terry Gross interview someone boring...it's easy to get interesting and gregarious people engaged in conversation, but much harder to get someone who's less so.

Hey Nick, when I spoke to you I got the same feeling I get from many supersmart codemonkeys with ideas on how to change the world - Damien Tew of the Embassy (I know you know Alton, so I assume you know him) and Jack Dorsey of Twitter both give me this sense as well. [I'm dead positive that Tynan is the same way, although I haven't met him. Then again, he does have pickup storytelling going for him....]

The feeling is that there are incredible things going on inside of your head, and that whenever you talk to me, you are putting those things on pause in order to address the conversation. Kind of like a patient parent who is explaining things to a child. It's not offensive, because its obvious you are not trying to do that and are indeed participating in a conversation with me, but it is there. Every moment you spend talking to me is an annoyance because it means you can't keep turning over whatever it is you are doing inside your mind.

Maybe its the intense, slightly vacant way you look at people while they're talking, and the measured, quiet way you put forth your own words, but I can't be sure. Perhaps look around a bit more instead of a laser focus gaze the whole time, and put a little bit of the passion I know you have for your interests into your words?

I only spoke to you once and it was a while ago, to be sure, but this is what I remember. Hope this helps in some way! It was still a great pleasure to get inside your world, even if only a little bit.

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After a reader asked about why I don't use shower products on the cold showers post comments, I started thinking of other things people do or use that I find I don't need. Here's a short list, preceded by a disclaimer: I'm not a joyless robot, deranged workaholic, or dirty hippy, so don't start with the pattern matching of stereotypes and questioning of my humanity. I just like to experiment.

Dessert. I randomly decided to only eat one dessert (the French macarons at my wedding) in 2013, and it has been great. It's simpler this way: I never have to resist eating desserts, and I appreciate tasty non-dessert food more. Drawback: sometimes I have nightmares where I accidentally eat a cinnamon roll, or some baddies are chasing me and trying to shove donuts into my mouth.

Drinking things that aren't water. From an early age I never wanted to try soda or coffee, and this persisted to never trying alcohol, either. I eventually accidentally had a digestif on a romantic date with Chloe in Paris, but it was gross. I stopped drinking fruit juice because it's too sweet, milk because of experiments with cutting out dairy, and vegetable juice because it gives me gas. What else do people even drink? Tea, I guess--I drink that when Chloe makes it, but I honestly don't see much difference between tea and hot water. It's just easier to be content with water than to ever crave some other sort of beverage.

Shower products. I gave more details in this comment, but basically I found that after five weeks of not using shampoo, my grease production shut down and I no longer needed shampoo (just like the internet said would happen). I tested body wash on one half of my body for a while and so no difference, so stopped that. I cut out conditioner when I cut off my long hair, and I use a dry-shave electric razor, so I never used shaving cream. Showers are now quite straightforward.

Recently I shared the benefits of smiling which include living longer, having happier marriages, and being perceived as more likable. These things all sounded great and I wanted to put them to the test, to smile at people and get a smile in return.

My first challenge was our youngest daughter. We were sitting down to a family dinner and she was pouting about either having to eat something she didn't want or not eat something she did want. That's how most of our food discussions at home go - not being served enough food from the marshmallow/chocolate food group. She sat there pouting and instead of explaining to her the virtues of micronutrients and why she couldn't have all the sugar she wanted, I smiled. I talked to the other members of our family and kept smiling - and it worked. Eventually she smiled back and began eating the peas she was refusing. Plus one for the power of smiling.

The next day I was picking her up from preschool and thought I would try to bring a bit of joy to her teacher. Being around 18 four-year-olds cant' be the most relaxing job one could have so she might need some of the endorphins I was inspiring. I waited in the line of parents to collect my daughter and when it was my turn I stepped to the door wearing a big smile like it was an "I Voted Today" button. It worked again! Though she is a cheery teacher and probably smiles alot, she wasn't smiling before I arrived and she was smiling after she met me. I think scientist call this a natural experiment, I'm calling it further proof that I can bring smiles to people. At this point I feel my power building.

Riding this high of success, a thought occurs to me. Maybe I'm playing in the minor leagues. What if my daughter and her plucky teachers are easy smilers. What if they smile all the time and they're already getting the benefits? I need to find people who need these smiles more. Luckily our little town has just the place.

We pull up to Taco Bell as a family the next day. Here I'll test my chops. Only the happiest people are going to be smiling working at Taco Bell during the lunch shift. I worked at Wendys during the lunch shift and the only time I smiled was when I was eating free food. This would be a blank slate attempt. I could safely assume there were no smiles there before me and I could test how many smiles were there when we left.